Azodyestuffs



Fatented Oct. 26, 1937 Ludwig Hauck, Leverkusen-I. G. Werk, Heinrich Clingestein, Cologne, and Fritz Graf, Leverkusen-I. G. Werk, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application January 23, 1937, Se-

rial No. 122,006. In Germany February 5,

4 Claims.

The present invention relates tonew tetrakisazodyestufis, more particularly it relates to azodyestuffs which may be represented by the following general formula:

In the said formula R1 and R2 stand for radicals of the benzene series bearing the azo group in para-position to the imino group, R3 and R4 stand for radicals of diazotized Z-aminonaphtholsulfonic acids, and R5 and Rs stand for radicals of meta-arylenediamines being at least once substituted in one amino group by a hydro-xyalkyl group, for example R5 and Rs each stands for the radical of meta-phenylenediamine which is substituted in one amino group by hydroxymethyl, hydroxyethyl, hydroxypropyl, a glycol radical, a glycerine radical and the like, or for a meta-phenylenediamine containing 7 in each amino group one of the afore-mentioned sub-' bloomy shade of the dyeings obtained therewith. The invention is illustrated by the .iollowing example: (the parts being by weight) Example 27.9 parts of 4,4-diaminodiphenylamine-2- sulfonic acid are tetra-zotized in the usual manner with 13.8 parts of sodium nitrite. The tetrazo compound is coupled in the customary manner in a medium alkaline with sodium carbonate with 4'7 .8 parts of 2-amino-S-naphthol-G-sulfonic acid. The dyestufi thus obtained is isolated, mixed with caustic soda lye while stirring, and 13.8 parts of sodium nitrite, and then 70 parts by volume of hydrochloric acid 19.5 B. are added. This tetrazotization mixture is added to a solution of 39.2 parts of hydroxyethyl-metaphenylenediamine and 60 parts of sodium carbonate. The coupling mixture thus obtained is heated to 95 C., and the dyestufi is salted out and squeezed. After drying the dyestufi which corresponds in its free state to the following stituents, or in which the two hydrogen atoms formula:

. N='- N=N N-OHn-OHpOH j Hogs NH:

Hotsl 40 N=N N= N-CHa-CHq-OH H03 NE,

of one amino group are substituted by these sub- 7 forms a dark powder, which dyes cotton and viscose bloomy black shades of good dischargeability.

When using instead of 4,l'-diaminodiphenylamine-2-sulfonic acid amine-3'--methyl-2-sulfonic acid or 4,4'-diaminodiphenylamine- 3 -methoxy- 2 -sulfonic a c i d, and/or instead of 2-amino-8-naphthol-6-sulfonic acid 2-amino-8-naphthol-3.6-disulfonic acid or 2-amino-5-naphtho1-7-sulfonic acid, and/or instead of the hydroxyethyl-meta-phenylenediamine wholly or partially its homologues and substitution products, as for example hydroxyethyl- 4,4'-diaminodiphenylmeta-toluylene-diamine, 1-chloro-2-amino-4-hyz ene series bearing the azo group in para-posh tion to the imino group, R3 and Ristancl for radi n cals of diazotized Z-aminohaphtholsulfonic ac- 7 properties are obtained;

' dyeing cotton generally ibloomy droxyethylaminobenieiie or 1(dihydroxypropy1- amino) -3-aminobenzene, dyestuffs of similar 7 We claim: 7 V

1. Tetrakisazodyestuffs of the following gen- V RFN='N R4',N=NER6 V wherein R1 and R2 stand for radicals of thebenids, and R5 and R6 stand for radicals of meta arylenediarnines being at least once substituted alkyl group, dyeing cotton generally bloomy black shades of good dischargeability.

3. Tetrakisazody'estufis having in the free state 7 the following general formula:

in one amino group by a hydroxyalkyl group;

good dischargeability.

the following general formula Hogs state the following formula:

' OH 7 V 1 1 V N=N N=N-NCH2OHOH Hogs NH: 7

'HOgS wherein R1 and R2 stand for radicals of the ben- 5 zene series bearing the azo groupin paraposi- 2.- Tetrakisazodyestuffs hav ng is the free state black shades of wherein R1 and R2 stand for radicals of metaarylenediamines being at'least once substituted 5 in one amino group by a: hydro'xyalkyl group, dyeing cotton generall'y'bloomy blackshades of' V dyeing cotton and viscose bloomy black shades of good dischargeability.

LUDWIG HAUCKc HEINRICH CLINGESTEIN. FRITZ GRAF. 

